Base Stabilization

[MedPR]

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Why does stabilization of a base make strengthen its conjugate acid?

All answers are accepted except for "weaker conjugate base = stronger conjugate acid." Thanks!

 

[chiddler]

Look at the opposite first. It's a stable base. So now we forcefully remove a proton from it. What will happen? It will want a proton back to bring it back to its stable form. The more stable it is when protonated, the stronger it will want the proton back. Which is why tbutyl lithium is a super base.

Now we force a proton onto the same stable base. It will give up the proton easily in order to revert to its stable form.

 

[mcloaf]

Well, picture an energy state diagram/thermodynamics graph of the conversion from acid to base. If the base is more stable, it will be lower on the energy axis and the deprotonation of the acid will release more energy.

 

[CodeRedDew]

Well "strength" of any acid is based on relative terms. There really is no cutoff for "strong" acids. So with that in mind, the strength of any acid is determined by the stability of its conjugate base. The reason is because for an acid to behave as an acid, it must donate its proton thereby turning it into its conjugate base. Therefore, the more "willing" it is to give up its proton, the stronger the acid is relative to an acid with a not-as-stable conjugate base. The acid with a not-as-stable conjugate pay pays a bigger fee energetically to give up its proton; therefore, the acid with a more stable conjugate base is more willing to give up its proton, ultimately making it a stronger acid relative to the other one.

 

[MedPR]

Thanks everyone 🙂 I was really wanting to get a few different perspectives on this topic so that I can see it in different ways just in case the question is confusing.